What Could Have Been
by Relativity1953
Summary: A quick look at 20 years in the lives of the Winchesters. Written for sams1ra, who gave me the prompt... Adam was born at the end of Sept... and 9 months before would have been January...


Prompt from sams1ra:

In 'Jump the Shark', we find out Adam's birthday is in the end of September. Which means, 9 months earlier was the end of January. In other words - not only did John miss Dean's birthday that year, but it's obvious he didn't just go from torn to hell in the ER to Kate's pants without some time to... uh... well. Anyway. John missed Dean's birthday for that. That's my bunny.

**Spoilers for**:

1.01 (Pilot), 1.18 (Something Wicked), 3.08 (A Very Supernatural Christmas), 4.19 (Jump the Shark)

*

**What Could Have Been**

November 1989

Dean knew he screwed up. Screwed up big time. It didn't take his father's hard glare and harsh words, or the silent car ride that took a little over three hours when it should have taken almost five, or the way Dad only checked Sammy in the rear view mirror and never once made eye contact with Dean, or even the way John rushed into Pastor Jim's place with a sleepy Sammy cradled in his arms... leaving Dean to get their bags and make his own way inside... or maybe that didn't even matter because as soon as Dean crossed the threshold to the inside, John pushed past him and crossed the threshold to the outside, hopped back in the Impala and sped away.

Yeah, Dean didn't need any of his father's actions to know how badly he screwed up. He was ten years old – almost eleven – and he's known about monsters since before he was five, when his dad went to see the psychic lady after his mother died. He's known about monsters – Dad called this one a Shtriga – for six years and he still left his baby brother, his responsibility, alone. Tonight, he almost killed his six year old brother out of carelessness because he was selfish and left him alone.

Dean Winchester was officially the worst big brother – the worst son – ever.

December 1989

The drive back to Fitchburg, then the return trip to Blue Earth left John Winchester tired, disordered, and angry. He tried to walk quietly in through the back door to the kitchen, but his coordination seemed to have stopped working for him. He had thought about staying the night back in Fitchburg but he really needed to get back and see how Sammy was doing. He told Jim as much when he found the man sitting at the kitchen table sipping a steaming mug of tea.

Jim told the travel-worn hunter that, having just checked in on the youngest Winchester, he could assure John that the boy was fine – gaining color in his cheeks even. The pastor was about to tell John that Dean had been awake the entire time his father was gone, watching his little brother and making sure he was all right, but Jim noticed that John had already left the kitchen for the spare room that had been set up for him. The pastor sighed and sipped his tea.

The Winchesters stayed with Jim for a month and, while Jim was happy to have them, he couldn't help the sad feeling settling in his bones. He was, of course, grateful that Sam seemed to come from his close encounter with the Shtriga with no ill after-effects and was quite happy with the attention he was getting from his oft-absent father. Dean, on the other hand, was quiet in a way Jim hadn't seen in years. The boy kept himself to the periphery, anticipating his brother and father's needs and making sure they were met without a word or worry – or even a wait.

After a month, just after Christmas, two Winchesters remained while their father left for Minnesota to look into a recent spate of grave robberies.

1 January 1990

Midway through another hectic holiday shift at the hospital, Kate caught sight of Joe practically dragging another man into the ER. Both men were slashed up to near ribbons, soaked with blood and melted snow. While the mystery man was whisked away up to surgery, Kate was treated to the tale of Officer Barton's adventures. As she cleaned Joe up, stitching him back together in a few places, he told the gathering crowd about a hero named John Winchester – a state marshal who had been called in to help him track down the grave robbers that had been making their way around Windom. He explained to the oohs and aahs of the random assembly how this champion had put himself between the monster and the lawman, taking him down when the culprit attacked them with two of the largest knives Joe had ever seen.

But there were two, and when the fiend's partner surprised them with much more hostility and accuracy, Joe was knocked to the ground, rolling down a hill and onto the frozen creek bed. As he carefully made his way to the edge of the ice, he noticed a gun on the shoreline – John's gun. The officer tried to climb back up the hill but, even though the snow had stopped coming down, the ground was still covered and the hillside was too slick, leaving John with no weapon or back-up. The only thing he could do was go the long way around as quickly and carefully as he could.

When he finally made it back to the crypt where the grave robbers had been hiding out, both of the villains were dead. Unfortunately, it looked as though John was gone as well. But, he knelt down next to the man that had saved his life – twice that night – and tried to find a pulse. He owed the man that much. And when he felt found that beat, he knew he had to bring the hero here – the best hospital around.

As dramatic as the tale became, Kate couldn't help but find herself wanting to know all about John Winchester.

5 January 1990

When John finally woke up (for more than a couple of minutes at a time), he was bleary-eyed and fuzzy-headed. He felt wrapped like a mummy and everything around him was too bright. But then, he saw an angel – and not just any angel, but Mary, the love of his life.

Mary took a step back when he called her by name, but he was not going to give up his chance to see his long-gone wife so easily. With his hunter reflexes, he reached out and caught her left hand in his and began speaking to her – not sure what he was even saying or if it was anything more than slurred mumbles. But, as Mary placed her right hand on his shoulder, still holding his hand with her left, he knew she could understand every word and drifted into the first truly peaceful sleep he'd had in years.

10 January 1990

John was awake and he was stable, and so hospital protocol said it was time for him to go. He had come to learn that his angel was not, in fact, Mary but a sweet nurse named Kate. Once his vision had completely cleared, he could see the differences right away – the most obvious being the eyes. Where Mary had calming and loving crystal blue eyes, Kate's eyes were honeyed hazel brown, sharp yet natural and uninhibited.

And, while calling a woman by the wrong name is usually grounds for a slap to the face, or at the very least an unpleasant and often loud scene, Kate became quite enchanted with John. Since the moment he awoke, she went out of her way to check on the man of mystery. They talked, learning things about one another and laughing like old friends. It had been a long while since John had felt so enlivened.

While John steered clear of anything too personal, he did tell Kate about his late wife. He left out anything that had to do with hunting in any way, but admitted to her that he had no one to pick him up from the hospital and that his plans included traveling to stay with a friend in a town over an hour away.

18 January 1990

John wasn't sure how it had happened. One moment, Kate was wheeling him to the exit of the hospital and the next she was helping to guide him to her car. Oh sure, he knew he was not supposed to put pressure or basically move his right leg until it healed up some, but the knowledge hadn't deterred him from planning to drive back to Blue Earth directly from the hospital.

Kate about had a fit, and before he even knew she had talked him into it, he was riding shotgun on the way to the woman's home. There was some talk of him needing to rest, of her being a nurse, and of her large home that had two spare bedrooms already made up just waiting for the opportunity to be used.

Before this ghoul hunt, John would have laughed at – or more likely punched – anyone who suggested he would look at another woman the way he had Mary. But, there was such a natural, easy affinity with Kate. And John couldn't help but let himself fall into the fantasy of what could have been – a world where demons and ghosts and monsters were still just stuff of stories and superstitious folklore.

24 January 1990

They had finally let down their barriers and allowed themselves to feel complete and whole with one another. Kate would always think of Wednesday, January 24, 1990 as their anniversary – the first time she and John made love.

31 January 1990

She knew it wouldn't last, that it wasn't a forever kind of thing. John had been completely honest about that. She knew he had a life somewhere, and that somewhere wasn't here. But for an entire week, John Winchester had been hers and she was happy for the time they shared.

1 February 1990

When John limped through his door, Jim had it on the tip of his tongue to be stern with the man. The boys had been on their absolute best behavior, but that was hardly the point. What sort of father leaves for a month without calling to check in, to explain, to wish his elder son a happy eleventh birthday?

He didn't back down because of the way John would react. The pastor had known the man for long enough and had seen the backlash aimed at anyone trying to give him parenting advice. And he didn't back down because of the state John was in. Again, the pastor had known John long enough and had seen him with all manor of injuries and illnesses – had actually administered his Last Rites not five years before. No, the reason Jim held his tongue was because the very second the door had closed, little Sammy was up and running joyfully for his daddy. And the look of pure happiness on John's face as he hugged Sammy to him was enough to silence Jim's tongue.

February 1990

The Winchesters remained with the pastor for the rest of John's recuperation. A member of Jim's congregation – kind, old Miss Rigby – offered to tutor Dean while the boy was away from school. Jim, unsure how well John would take the proposal, was about to give the retired school marm a quick 'thanks but no thanks' when Dean spoke up and agreed.

For the rest of their stay in Blue Earth, Dean dedicated himself to his studies in the same way he had always dedicated himself to his family. If John noticed the uncharacteristic behavior, he never mentioned it.

March – July 1990

As soon as he was back to full strength and completely recovered from the run-in with the ghouls, John uprooted his family from Minnesota for a hunt down in Mississippi. It was a fast-paced five months but the family took everything in stride. Dean had been to three different schools in as many months and he was actually keeping up with his classes.

Dean also seemed to be keeping up with his chores without any incident and John found that his weapons were always in tip-top shape. He had never seen his son actually cleaning the weapons – and he had better not be doing so in front of Sammy...

August 1990

Just yesterday, Sammy was a toddler, barely able to walk without falling down every third step. Yet, today Dean told John that Sammy needed to be enrolled in school. Time sure did fly.

29 September 1990

Kate could hardly believe it when she found out in March that she was pregnant. Even more surprising were the labor pains that awoke her at 4:51 a.m. on September 29. Her due date was October 17. As far back on her family tree as she knew, no Milligan had ever arrived even a week after they were supposed to. Trust her son to be early.

In the back of her mind, she wished she had stayed in touch with John.

November 1990

John wasn't sure what he had been afraid of. Sammy had seemed so young, so small to be starting school. John was worried how the boy would handle being around so many new people, how he would get to and from school, if he would be able to keep up with his work while on the road. He shouldn't have worried. His boy was so smart that, after a month, Miss Charlotte – Sammy's teacher – had called to meet with John to see how he would feel about moving the boy up a grade.

He just knew Sammy was going to be brilliant.

December 1990

For over a year, Dean had been trying his hardest to regain his father's trust and love. He had done everything he'd been told and then some. He'd trained and cleaned weapons and made meals and done his homework without complaint. He had made sure Sammy, not only got to school, but to his classroom and was outside the room waiting for him when the afternoon bell rang. He had watched out for Sammy at school, made sure he did his homework (and checked it over), and packed his lunches every day. He had even been able to save some of his own lunch money to pay for Sammy's new clothes and birthday and Christmas gifts.

However, when John dropped the boys off with Pastor Jim and left for a hunt just two weeks after New Year's, Dean was positive it hadn't been enough.

20 January 1991

John had just wanted to stop by and see how she was doing. He didn't want to intrude upon Kate's life anymore than he already had, but she turned and spotted him before his hunter instincts had been able to kick in. He had a pretty good excuse for that though – he hadn't been expecting the baby in her arms.

She smiled when she saw him, not the least bit angry or annoyed, as she unbuckled Adam from his car seat. Shivering, she motioned for John to follow her, inviting him into her home (again). When they were all warm once more, Kate introduced John to their son.

26 January 1991

John had used the excuse of a quick hunt before leaving the boys with Jim as he checked in on Kate. After the heart-warming discovery of another son and a woman that still loved him, John knew he needed to call and tell Jim that the hunt was taking a new turn and that it would be at least another week – maybe two – before he could get back.

As Jim hung up his phone, Dean entered the kitchen. There was no need to explain to the boy, as he had overheard the end of Jim's half of the conversation with John. Jim wanted so badly to give Dean some sort of hope – the boy seemed so disappointed.

What Jim didn't know – couldn't have known – was that Dean's disappointment wasn't with John missing his birthday once again. Dean was disappointed in himself. Obviously, he hadn't proven himself worthy enough yet.

Mid-December 1991

Nothing had really changed in a year. But, when John left the boys by themselves in a little run-down motel in Broken Bow while he went on a hunt for a revenant Dakota City, Dean had mixed feelings. It was nice to feel that his father trusted him enough again to leave him in charge when gone for more than two days. However, he was worried about his dad missing Christmas – for Sam.

Mid-January 1992

The revenant hunt had been tougher than he had anticipated. John hated that he missed Christmas with his boys but the past could not be changed. He comforted himself in the fact that he had saved two whole (and still innocent) families during this hunt.

He also decided to swing by and visit Kate and Adam for a few days.

24 January 1992

John was home in time for Dean's birthday this year, however, it seemed to pass without notice. But that was all right. Dean decided he was too old to celebrate birthdays anymore.

February 1992

Just as life seemed to be getting back to normal, Sammy confronted John about his 'real' business. Well, Dean thought to himself as their father looked over at him with disappointment clearly written on his face, his little brother had lasted almost two whole months.

February 1992 – September 2001

For nearly ten years, John trained Mary's boys in all manner of combat, with all manner of weapons, so that they were ready to take on all manner of supernatural monsters. All the while both of the boys excelled, but while Dean took instruction and orders obediently, Sammy – Sam – became more and more argumentative. John had to admit that the boy reminded him of himself at that age and he was proud of his son for having his own mind, but at the same time he was getting more and more frustrated with Sam.

Sam didn't like or agree with his father's 'do as I say not as I do', 'my way or the highway' way of doing things. He couldn't just sit mindlessly by – resenting his older brother more and more for doing just that – and accept what he was told without question. He noticed his father always took on solo hunts whenever they were near Iowa or Minnesota, but his questions about it were always outright ignored.

The inevitable war between John and Sam finally came to a head when John found his son's admission letter to Standford. He could not have been more proud of the kid for not only getting into the prestigious school, but for getting a full ride as well. However, his fear of what could and would happen overrode his awe and, after sending Dean out for dinner, he laid in wait for Sam.

Dean was walking up to the front door of the shack the Winchesters were currently calling home just as Sam exited with his duffel bag, slamming the door as hard and loud as he could. When Dean asked his kid brother what had happened this time, Sam threw some cryptic remark – The wind of freedom blows – over his shoulder and was gone.

A week later, Dean discovered that _Die Luft der Freiheit weht_ – German for "The Wind of Freedom Blows" – was the motto of Stanford University.

September 2002

The distance between John and Dean had been growing over the last year. They were spending more and more time apart – due to John setting them up with individual hunts. If Dean had been honest with himself, he would have acknowledged he was uneasy – a little frightened even – by his dad's enforced separation. And then came the two months without any visual contact.

29 September 2002

When Adam turned twelve, he got the best birthday present ever. He finally got to meet his dad.

The funny thing was, he had seen the man before. Several times over the years in fact. He first noticed the man when he felt someone watching him and his mom, and turned to see Mom smile at a man he had never met. The man smiled back but kept his distance and Adam noticed the calm and happiness that washed over his mom. Soon, the man's presence made him feel the same way.

It was a little strange to find out this man was his dad. He wanted to ask so many questions but he didn't want to burst the bubble of euphoria that surrounded them. So, like his mother, he learned to enjoy whatever time he had with John Winchester.

24 January 2004

Dean was spending more time communicating with his father through cell phone messages than getting to talk with the man himself. The few times he had tried to call Sam had been the same way. Then, there was the message he had just listened to.

After calling Sam's dorm room and talking to the kid's roommate – Sam should be back soon; he was on a date with his girlfriend; it was her birthday today – he left a simple message for him to call Dean.

Dean had been surprised when he got out of the shower and found that he had a message already. More surprising was the message itself, Sam's long-suffering voice telling him to stop calling.

31 October 2005

It was too much. First the lack of visual contact, then the phone-tag conversations, and now there was absolutely nothing. Dad was supposed to have called him no later than October 1. The last time he got a message was the completely distorted, half unintelligible voice mail full of EVP.

He had tried to keep away. Sammy didn't want him around and for almost two years he had respected those wishes. But now he needed help. Sure, he changed the dates up a little – Sam didn't need to hear Dean whine about his general miserableness at being completely abandoned by both members of his family.

29 September 2006

The last time Adam saw his father was on his sixteenth birthday. Had he known it would be the last time, he probably would have asked John all the questions that had been floating around in his head for the past four years. Or, at the very least, done something more personable. Of course, the baseball game had been really fun.

17 April 2009

Adam had been unable to get a hold of his mother all week. After his last class on Friday, he drove home to try and find out what was going on. Unfortunately, something found him first.

21 April 2009

When Dean and Sam got the call from someone claiming to be John Winchester's son, Dean didn't believe him for an instant. Sam went into research mode and found that there was a definite possibility that this Adam Milligan was telling the truth.

Checking out the kid's house was surreal. There were framed pictures of John Winchester smiling – completely carefree – with his arm around a woman that was not Mary. There was one of Adam holding some sort of fish while John held two fishing poles. And, Dean noticed towards the back of Kate's nightstand, there was a picture of the couple with a banner behind them reading 'Happy Fifth Anniversary!' The time-stamp in the corner said '01/24/05.'

23 April 2009

Although Adam's story about John turned out to be true, Dean and Sam had found out too late about their half brother. The kid and his mom had been killed before the Winchesters had even arrived in Windom. As they watched the body of the brother they never knew burn on the funeral pyre, the Winchester brothers mourned not the loss of more family, but the loss of what could have been.


End file.
